Surfing NSW Chemistry Modules 7-8

192 Pages·2018·154.849 MB·English

by  Marilyn Schell, Margaret Hogan

© Science Press 2018
First published 2018
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Contents
Introduction V Alcohols
Words to Watch vi INQUIRY QUESTION
How can alcohols be produced and what are their
Module 7 Organic Chemistry properties?
29 Alcohols 50
30 Enthalpy Of Combustion Of Alcohols 52
Nomenclature
31 Reactions Of Alcohols 54
INQUIRY QUESTION
32 Production Of Alcohols 56
How do we systematically name organic chemical
33 Biofuels 57
compounds?
34 Biagas 59
1 The Element Carbon 2 35 Bioethanol and Biodiesel 60
2 Organic Chemistry 3 36 Comparing Fossil Fuels and Biofuels 62
3 Hydrocarbons - Alkanes 5 37 Petrodiesel and Biodiesel As Transport Fuels 64
4 Hydrocarbons - Alkenes 7 38 Revision Of Alcohols 66
5 Hydrocarbons - Alkynes 8
6 Naming Hydrocarbons 9 Reactions Of Organic Acids and Bases
7 Alcohols 12
INQUIRY QUESTION
8 Carboxylic Acids 13
What are the properties of organic acids and bases?
9 Aldehydes and Ketones 15
10 Amines and Amides 16 39 Aldehydes and Ketones 68
11 Halogenated Organic Compounds 17 40 Amines and Amides 69
12 Structural Isomers 19 41 Carboxylic Acids 70
13 Revision Of Nomenclature 21 42 Comparing Homologous Groups 72
43 Esters 75
Hydrocarbons 44 Esterification 77
45 Organic Acids and Organic Bases 78
INQUIRY QUESTION
46 Hydrolysis Of Esters 79
How can hydrocarbons be classified based on their
47 Soaps 80
structure and reactivity?
48 Detergents 83
14 Models Of Hydrocarbons 23
49 Organic Reaction Pathways 85
15 Revision - lntramolecular Forces 24
50 Revision Of Reactions Of Organic Acids and Bases 87
16 Revision - Intermolecular Forces 26
17 Revision - More Intermolecular Forces 28
Polymers
18 Properties and Bonding Of Hydrocarbons 29 EGM&fMi.¾¥#1
19 Shapes Of Hydrocarbon Molecules ~
20 Safety With Organic Compounds 33 What are the properties and uses of polymers?
21 Revision - Fossil Fuels 34 51 Monomers and Polymers 90
22 Revision - Fractional Distillation 37 52 Polyethylene and Its Production 91
23 Revision - Products Of Combustion Of Fossil 39 53 Other Addition Polymers 93
Fuels 54 Condensation Reactions 95
24 Revision - The Greenhouse Effect 41 55 Condensation Polymers 96
25 Revision Of Hydrocarbons 43 56 Thermoplastic and Thermosetting Polymers 98
57 Designing Polymers 99
Products Of Reactions Involving Hydrocarbons 58 Advantages and Disadvantages Of Polymers 101
59 Revision Of Polymers 105
INQUIRY QUESTION
What are the products of reactions of hydrocarbons and 60 Revision Of Organic Chemistry 107
how do they react?
26 Substitution Reactions 45
27 Addition Reactions 47
28 Revision Of Products Of Reactions Involving 49
Hydrocarbons
Science Press MODULE 7 ORGANIC CHEMISTRY
Surfing NSW Chemistry Modules 7 and 8 MODULE 8 APPLYING CHEMICAL IDEAS Ill
Chemical Synthesis and Design
Module 8 Applying Chemical Ideas
INQUIRY QUESTION
What are the implications for society of chemical
Analysis Of Inorganic Substances
synthesis and design?
INQUIRY QUESTION
83 Chemical Resources 167
How are the ions present in the environment
84 Industrial Chemistry 168
identified and measured?
85 Chemical Synthesis 170
61 Introduction To Inorganic Analysis 112
86 Reactants, Products and Reaction Conditions 172
62 Water Pollution and Monitoring 113
87 Stoichiometry and Yield 173
63 Collecting and Testing Water Samples 117
88 Atom Economy 175
64 Atmospheric Pollution and Monitoring 119
89 Green Chemistry 176
65 Flame Tests 121
90 Synthesis Of Soap 179
66 Using Solubility Rules 122
91 Carbohydrates 180
67 Complex Ions 125
92 Revision Of Synthesis and Design 185
68 Gravimetric Analysis 127
93 Revision Of Applying Chemical Ideas 186
69 Precipitation Titrations 128
70 Colorimetry and UV Visible Spectrometry 129
Topic Test 189
71 Atomic Absorption Spectroscopy 133
Answers 194
72 Revision Of Analysis Of Inorganic Substances 136
Formula Sheet 246
Data Sheet 246
Analysis Of Organic Substances
Periodic Table 249
INQUIRY QUESTION Index 250
How is information about the reactivity and structure
of organic compounds obtained?
73 Sources Of Organic Pollution 139
74 Chemical Tests For Functional Groups 141
75 Mass Spectroscopy 144
76 Infra-Red spectroscopy 149
77 Introduction To NMR 153
78 Nuclear Magnetic Resonance 155
79 Chromatography 158
80 Calibration Curves For Chromatography 161
81 Combining Analytical Methods 163
82 Revision Of Analysis Of Organic Substances 164
MODULE 7 ORGANIC CHEMISTRY Science Press
iv MODULE 8 APPLYING CHEMICAL IDEAS Surfing NSW Chemistry Modules 7 and 8
Introduction
This book covers the Chemistry content specified in the NSW Chemistry Stage 6 Syllabus. Sample data has been
included for suggested experiments to give you practice to reinforce practical work in class.
Each book in the Surfing series contains a summary, with occasional more detailed sections, of all the mandatory parts
of the syllabus, along with questions and answers.
All types of questions - multiple choice, short response, structured response and free response - are provided.
Questions are written in exam style so that you will become familiar with the concepts of the topic and answering
questions in the required way.
Answers to all questions are included.
A topic test at the end of the book contains an extensive set of summary questions. These cover every aspect of the
topic, and are useful for revision and exam practice.
Science Press MODULE 7 ORGANIC CHEMISTRY
Surfing NSW Chemistry Modules 7 and 8 MODULE 8 APPLYING CHEMICAL IDEAS V
Words To Watch
account, account for State reasons for, report on, give explain Make something clear or easy to understand.
an account of, narrate a series of events or transactions.
extract Choose relevant and/or appropriate details.
analyse Interpret data to reach conclusions.
extrapolate Infer from what is known.
annotate Add brief notes to a diagram or graph.
hypothesise Suggest an explanation for a group of facts
apply Put to use in a particular situation. or phenomena.
assess Make a judgement about the value of something. identify Recognise and name.
calculate Find a numerical answer. interpret Draw meaning from.
clarify Make clear or plain.
investigate Plan, inquire into and draw conclusions
classify Arrange into classes, groups or categories. about.
comment Give a judgement based on a given statement justify Support an argument or conclusion.
or result of a calculation.
label Add labels to a diagram.
compare Estimate, measure or note how things are
list Give a sequence of names or other brief answers.
similar or different.
measure Find a value for a quantity.
construct Represent or develop in graphical form.
outline Give a brief account or summary.
contrast Show how things are different or opposite.
plan Use strategies to develop a series of steps or
create Originate or bring into existence.
processes.
deduce Reach a conclusion from given information.
predict Give an expected result.
define Give the precise meaning of a word, phrase or
propose Put forward a plan or suggestion for
physical quantity.
consideration or action.
demonstrate Show by example.
recall Present remembered ideas, facts or experiences.
derive Manipulate a mathematical relationship(s) to give
relate Tell or report about happenings, events or
a new equation or relationship.
circumstances.
describe Give a detailed account.
represent Use words, images or symbols to convey
design Produce a plan, simulation or model.
meaning.
determine Find the only possible answer.
select Choose in preference to another or others.
discuss Talk or write about a topic, taking into account
sequence Arrange in order.
different issues or ideas.
show Give the steps in a calculation or derivation.
distinguish Give differences between two or more
different items. sketch Make a quick, rough drawing of something.
draw Represent by means of pencil lines. solve Work out the answer to a problem.
estimate Find an approximate value for an unknown state Give a specific name, value or other brief answer.
quantity. suggest Put forward an idea for consideration.
evaluate Assess the implications and limitations. summarise Give a brief statement of the main points.
examine Inquire into. synthesise Combine various elements to make a whole.
MODULE 7 ORGANIC CHEMISTRY Science Press
Vi MODULE 8 APPLYING CHEMICAL IDEAS Surfing NSW Chemistry Modules 7 and 8
NSW CHEMISTRY
In this module you will:
• Focus on the principles and
applications of chemical
synthesis in organic chemistry,
including pharmaceuticals, fuels
and polymers.
• Investigate the naming, structure
and classification of organic
chemicals.
• Investigate the characteristic
chemical properties and
reactions of classes of organic
compounds based on their functional groups.
• Consider the primary, secondary and tertiary structures of organic materials and how this
affects properties such as strength, density and biodegradability of proteins, carbohydrates
and synthetic polymers.
1 The Element Carbon Note: Although the electrons in all atoms are identical,
they are sometimes illustrated as crosses and dots as in
Figure 1.2 to show that the two electrons in a bond come
Carbon is a non-metal element. Its atomic number is
from different atoms.
6 because it contains 6 positively charged protons in the
nucleus of each atom. There are also 6 negatively charged These are all strong covalent bonds and they increase in
electrons orbiting the nucleus, with two electrons in the first strength from single C-C bonds to double C=C bonds,
shell and four electrons in the outer shell. So the electron with the shortest and strongest being triple C=C bonds.
configuration of carbon is 2.4 and it has a valency of 4.
Table 1.1 Bond energies between carbon atoms.
I
----<>---- Nucleus containing Bond Bond energy (kJ mol-1)
------&--___ _ 6 protons and 6 neutrons Single bond: C-C 348
Double bond: C=C 614
" ~ Triple bond: C=C 839
.,..__~ 6 electrons orbit
'' ' the nucleus Carbon also bonds with other elements. It forms strong
covalent bonds with hydrogen atoms. These are
considered to be non-polar bonds as the electronegativity
difference between the atoms involved is very small.
Carbon also forms stable polar bonds with oxygen,
Figure 1.1 Atom of carbon-12. nitrogen, phosphorus and the halogens.
Carbon is a special element because of the millions of You already know that the Table 1.2 Bond energies
compounds it can form and because carbon compounds are strength of these bonds between carbon and some
important constituents ofliving as well as non-living things. varies with such factors as other atoms. {These vary
slightly in different sources.)
The huge number of carbon compounds in existence is length of bonds (strength
due largely to its ability to form strong bonds with other increases as length Bond I Bond energy
carbon atoms, making chains and rings, and also the decreases) and differences (kJ mol-1)
stable bonds it can form with other elements. in electronegativity C-H 414
( strength increases as
C-0 358
electronegativity difference
Bonding of carbon atoms
increases). For example, C-N 305
Carbon atoms bond to each other by sharing electrons, bond energy between C-F 485
forming strong covalent carbon-carbon bonds. You carbon and the halogens
saw this last year when you studied carbon allotropes - decreases down the C-CI 339
diamond, graphite and fullerenes. halogen group. C-1 238
You will recall that carbon-carbon bonds can be single,
double or triple bonds. Single bonds are the most common. QUESTIONS
Ethane Ethene 1. (a) Outline the position of carbon on the periodic
H H H H table and state its electron configuration.
H•xCX xxCX x•H or H- 6-6-H (b) How many valence electrons are present in
I
~~ /~ HI each atom of carbon?
2. List four factors that contribute to the huge number
Single covalent bond Double covalent bond of carbon compounds that exist.
(1 pair of electrons shared) (2 pairs of electrons shared)
3. (a) Describe the type of bonding that occurs
between carbon atoms.
Ethyne
(b) Distinguish between single, double and triple
XX
H•xCg Cx-H or carbon-carbon bonds.
l
4. (a) Name three other elements that bond to carbon
atoms.
Triple covalent bond
(3 pairs of electrons shared) (b) Identify two factors than can determine the
strength of the bonds between atoms of carbon
Figure 1.2 Single, double and triple C-C bonds.
and other elements.
MODULE 7 ORGANIC CHEMISTRY
Science Press
2 MODULE 8 APPLYING CHEMICAL IDEAS Surfing NSW Chemistry Modules 7 and 8
2 Organic Chemistry
Organic chemistry is the chemistry of carbon and its
compounds. Carbon compounds are involved in our
everyday life - the food we eat, fuels we burn, our
own structure, and the polymers that we use to make
everything from clothing to cars - all of these are carbon
compounds.
Figure 2.2 August Kekule and Archibald Couper.
Their work represents the beginning of the concept of
bonds between the elements in a compound, and they
developed their ideas before anything was known about
the attractions between atoms forming bonds.
Today the atomic model and models of bonding are used
to explain the structure and properties of both elements
and compounds. Models and theories of the structure of
Figure 2.1 Carbon fibre is used in car bodies.
molecules have developed using evidence from a range of
Organic compounds make up over 80% of all known sources. And they can be used to explain and predict the
compounds and this does not include compounds such as properties of substances.
carbon oxides and carbonates. Organic chemicals include
Data from analytical techniques such as mass
the homologous series of alkanes and alkenes that you
spectrometry and crystallography have given us a deeper
learned about in year 11 as well as many other groups of
understanding of bonding and the chemical structure of
carbon compounds which are involved in everyday life
carbon compounds and we classify organic molecules
such as alcohols, proteins, fats, carbohydrates, polymers
according to the functional groups that they contain.
and many more.
Conversely, if we know the formula of an organic
You will recall that alkanes and alkenes have functional compound then we can predict its chemical behaviour
groups (C-C for alkanes, C=C for alkenes). In this section based on what we know about the behaviour of the
you will be looking at more series of organic molecules functional groups it contains.
that have other functional groups attached - the alcohols,
--carbux:ylic-acids;-esters;-amirres-and-amides-:-You---wi.11-be
Functional groups
seeing how the molecular structure of organic compounds
and also the presence of functional groups are related to A functional group is a specific group of atoms, within a
their properties. Later you will be looking at structures of molecule, that is responsible for the chemical reactions of
proteins, carbohydrates and polymers. that molecule.
The two scientists most influential in the initial Functional groups are attached to the hydrocarbon
development of carbon chemistry were a German 'backbone' of organic molecules. Figure 2.3 gives some
chemist August Kekule ( 1829-1896) and a Scottish examples of functional groups in organic compounds.
chemist Archibald Scott Couper (1831-1892). Based You need to learn these.
on their observations of reactions, these two chemists
The hydrocarbon backbone of organic compounds is
independently developed a theory of how carbon formed
represented by R in general formulas. An R can be added
bonds. They proposed that carbon was tetravalent to the functional groups to indicate the position of any
(valency of 4) and described carbon atoms linking to each attached hydrocarbon chain. If there is more than one
other, as well as to other atoms, and forming chains and
hydrocarbon chain, the chains are shown as R1, R2, R3.
nngs.
Alternatively dashes may be used, e.g. R', R", R'".
Science Press MODULE 7 ORGANIC CHEMISTRY
Surfing NSW Chemistry Modules 7 and 8 MODULE 8 APPLYING CHEMICAL IDEAS 3
Alkyl group
Alcohol Carboxylic acid
Another term you should recall is an alkyl group. This
-OH - C-OH
refers to a hydrocarbon chain with the general formula
II
Alcohol functional group 0 CnH2n+ 1• An example is a methyl group (--CH3). This is a
General formula of compound: Carboxylic acid functional group fragment of a methane molecule (CH4). Alkyl groups do not
exist on their own, they are branches of carbon molecules.
R-OH
General formula of compound:
R-COOH
Table 2.2 Alkyl groups.
Ester Amide I I I
Alkane Formula Alkyl group Formula
-C- 0- H
II I Methane CH4 Methyl group -CH3
0 - C- N-H
Ethane CH CH Ethyl group -CH CH
II 3 3 2 3
Ester functional group 0 Propane CH CH CH Propyl group -CH CHCH
3 2 3 2 2 3
General formula of compound: or-C H
Amide functional group 3 7
R1-COO-R2
General formula of compound:
R-CO-NH QUESTIONS
2
Amine Aldehyde
1. (a) Define organic chemistry.
H - C-H (b) Name five examples of organic compounds.
I II 2. Identify two chemists influential in the initial
-N-H 0
development of carbon chemistry.
Amine functional group Aldehyde functional group 3. (a) Define a functional group.
(b) Recall the functional group for an alkene, an
General formula of compound: General formula of compound:
R-NH R-CHO alcohol and a carboxylic acid.
2
4. What does IUPAC stand for?
Figure 2.3 Functional groups.
5. (a) What is meant by a general formula?
(b) Distinguish between the general formula for an
Homologous series alkane and an alkene.
6. What is meant by an homologous series? Include an
Organic compounds containing only carbon and
example in your answer.
hydrogen atoms are called hydrocarbons. Each family of
7. (a) What is meant by an alkyl group?
hydrocarbons is called an homologous series.
(b) Distinguish between butane and butyl.
Homologous means that all members of a series have
8. Check your knowledge with this quick quiz.
something in common - they share a general formula
(a) Hydrocarbons with single C-C bonds are called
and a special feature or functional group ( a grouping of
(alkanes/alkenes).
atoms that is common to all members of that series).
(b) The stem (prefix) of a carbon compound
There are three homologous series of hydrocarbons: with four carbon atoms would be named
• Alkanes have only single -C-C-bonds.
( c) The carbon atom attached to a functional group
• Alkenes contain at least one double -C=C-bond.
is numbered so that it has the (lowest/highest)
• Alkynes contain one or more triple -C=C-bond. possible number.
( d) State the general formula for an alkane.
Table 2.1 Three homologous series.
(e) The symbol R-OH is the general formula for
Homologous General an
I I Functional group
series formula ( f) Which part of the name of a compound tells
-C-C- you the functional group present?
Alkane CnH2n + 2 Single bonded carbon atoms (g) What is the stem (prefix) of an alkane with two
carbon atoms present?
-C=C-
Alkene CnH2n
Double bonded carbon atoms
-C=C-
Alkyne CnH2n-2 Triple bonded carbon atoms
MODULE 7 ORGANIC CHEMISTRY Science Press
4 MODULE 8 APPLYING CHEMICAL IDEAS Surfing NSW Chemistry Modules 7 and 8